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Road trip from Chicago to Staten Island
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ITINERARY
15h 0m792 miles24 stops
1
Michigan Avenue Bridge
The view from the bridge is one of the best vistas the city has to offer.
2
Boystown
Located in Chicago's North Side, this vibrant neighborhood is known for its exciting nightlife and for being one of the largest LGBTQIA+ communities in the city. It's the host of the annual Chicago Pride Parade, and a must-see in the area is the Legacy Walk on Halsted Street, where you can learn about the contributions of the LGBTQIA+ community while admiring the colorful street art and rainbow crosswalks. Check out the unique shops and then grab a bite at one of the area's delicious Thai or Mexican restaurants. At night, visit one of the neighborhood's bars to enjoy a drag show, concert, and tasty cocktail. Consider taking a food or walking tour of Chicago that stops by Boystown. – Tripadvisor
3
Wrigley Field
Get a behind-the-scenes look at the legendary home of the Chicago Cubs with Wrigley Field Tours. Built in 1914, this must-see Chicago attraction houses more than 100 years of history. New this year, fans can join us on a non-gameday Ivy Tour which includes the opportunity to take a photo in front of Wrigley Field’s historic ivy wall.
4
Allen County War Memorial Coliseum
5
Lakeside Park & Rose Garden
6
Amherstburg Navy Yard National Historic Site
7
Sprucewood Shores Estate Winery
The Sprucewood Family warmly welcomes you to sample handcrafted 100% Ontario VQA wines at Ontario's only beachfront destination vineyard, winery and tasting room. We are situated on 45 Acres with access to gardens, a sandy beach, and picnic tables. Enjoy a glass of wine with a picnic basket and explore our grounds year round. Tasting room open 7 days a week 11am - 5pm (we occasionally close early due to special events. Please check our social media for daily updates @sprucewoodshores)
8
Rock & Roll Hall of Fame
Headquartered in a boldly designed building on Lake Erie's shore, The Rock and Roll Hall of Fame is a 150,000-square-foot museum featuring ever-changing exhibits documenting the history of rock and roll, from Elvis to our days. You’ll see hundreds of original artifacts, from Jimi Hendrix outfits to The Beatles’ handwritten lyrics. Experience the excitement of a Rock Hall induction night at the Power of Rock Experience or have your very own jam session at the Garage. You can also watch a concert while you're here, so check out the Rock Hall’s schedule and plan ahead. – Tripadvisor
9
Federal Reserve Bank of Cleveland: Education and Learning Center
Ever wonder how money works or what the Federal Reserve Bank of Cleveland does as part of the central bank of the US? Visit our Education and Learning Center featuring more than 25 fun, hands-on exhibits that answer these questions and more! We have interactive games, visual exhibits, creative stations, and illuminating films that explain everything about money you can think of, from how we use it, to why it looks the way it looks. Come see our historic lobby, take pictures with our money tree, trade coconuts on Barter Island, identify counterfeit bills, and even make your own money! All this in the heart of Cleveland, just steps away from downtown attractions. Admission is free and photos are welcome.
10
Museum of Contemporary Art Cleveland
11
Lock 3
12
Paladin Brewing
13
Hollywood Gaming Mahoning Valley Race Course
14
Basilica of Our Lady of Mount Carmel
15
What Lifts You Mural
You can find one of the town’s most famous photo ops in The Gulch neighborhood—a pair of intricate white lace wings against a black wall. There's usually a line, so go early in the morning or late in the day for fewer crowds. Try to find the easter eggs that the artist put into the mural: a cowboy hat, guitars, and barbecues to represent Nashville. Explore other street art in Nashville on a mural art tour—you'll see lots of other great sights, with plenty of time for photo ops.
16
ScareHouse
Pittsburgh Zombies love shopping malls – and we think you will love our NEW, larger, and permanent home inside the Galleria at Pittsburgh Mills. Thank You Pittsburgh for supporting us for more than 20 years of fears! ScareHouse has been ranked as one of “America’s Scariest Halloween Attractions” by Travel Channel and has been featured on Good Morning America, USA TODAY, The Daily Show and many other national media outlets.
17
Marine Corps League NE Detachment Museum
18
Allentown Rose Gardens
19
Mack Trucks Historical Museum
20
Accomplice New York
This comedic interactive experience sends you on a mission to assist a bunch of ex-cons lookin’ to skip town. The journey starts near the South Street Seaport and works its way up through some of New York City's most colorful neighborhoods. Several alcoholic beverages and light appetizers are included during this three hour journey. For private groups, you can book up to 15 people. Basic pricing per person is $85.00. Accomplice also runs a Village show, a Chelsea show and a traveling meal, each with its own characters and story line. For more information, please visit our website!
21
BrainXcape
22
Precision NY Chauffeur & Airport Transportation Services
Here at Precision NY Chauffeur & Airport Transportation Service, we offer limousine service and point to point transportation NYC. You can always depend on us for reliable transportation New York, New Jersey, Westchester, Connecticut, Washington DC, Pennsylvania, and Boston. Along with equitable rates and attentive service, we offer transfer services anywhere within the country. For your convenience, you may reserve any vehicle from our fleet vehicles up to 24 hours in advance, including the Lincoln MKT, Lincoln Town Car and Cadillac XTS. For larger parties or a more comfortable ride, we have Cadillac™ Escalades, Lincoln™ Navigators, and Chevy™ Suburbans. We also carry New 2023 and 2024 Mercedes S560s.
23
The Blue Bar, Algonquin Hotel
Comfortable and classic, the lounge of the Algonquin Hotel is a New York landmark.
24
Daniel Roy's Parlour Of Deceptions
Join magician Daniel Roy at the exclusive Salmagundi Club of New York City for an evening of sleight-of-hand, misdirection, and magic. Limited to just 40 guests, this is an intimate experience of wonder. While this is not a kids show and the magic is geared towards adults, the performance is entirely “clean” and appropriate for audience members age 13 years and older.
Customize this Trip
OVERVIEW
Buckle up for an epic adventure that will take you from the bustling streets of the Windy City to the iconic shores of Staten Island! Along the way, you'll traverse vast landscapes, marvel at architectural wonders, and soak up the vibrant culture that defines America.
Your journey begins in the heart of Chicago, where towering skyscrapers paint the skyline. From there, you'll embark on a thrilling train ride across the sprawling Midwest, passing through charming towns and rolling hills. As you approach the Atlantic coast, the terrain transforms into lush forests and sparkling waterways.
Finally, you'll arrive at Staten Island, a vibrant tapestry woven with history, immigration, and modern-day allure. This unique borough offers a glimpse into New York City's past and present, with its historic landmarks, diverse neighborhoods, and breathtaking views of the Manhattan skyline. From the bustling streets of Chinatown to the tranquil shores of South Beach, Staten Island is a melting pot of cultures and a testament to the American spirit.
1
Start:Michigan Avenue Bridge
Chicago, Illinois·
4.5
(985) review
The view from the bridge is one of the best vistas the city has to offer.
2
Start:Boystown
Chicago, Illinois·
4.5
(98) review
Located in Chicago's North Side, this vibrant neighborhood is known for its exciting nightlife and for being one of the largest LGBTQIA+ communities in the city. It's the host of the annual Chicago Pride Parade, and a must-see in the area is the Legacy Walk on Halsted Street, where you can learn about the contributions of the LGBTQIA+ community while admiring the colorful street art and rainbow crosswalks. Check out the unique shops and then grab a bite at one of the area's delicious Thai or Mexican restaurants. At night, visit one of the neighborhood's bars to enjoy a drag show, concert, and tasty cocktail. Consider taking a food or walking tour of Chicago that stops by Boystown. – Tripadvisor
3
Start:Wrigley Field
Chicago, Illinois·
4.5
(9953) review
Get a behind-the-scenes look at the legendary home of the Chicago Cubs with Wrigley Field Tours. Built in 1914, this must-see Chicago attraction houses more than 100 years of history. New this year, fans can join us on a non-gameday Ivy Tour which includes the opportunity to take a photo in front of Wrigley Field’s historic ivy wall.
4
Start:Allen County War Memorial Coliseum
Fort Wayne, Indiana·
4.0
(99) review
4000 Parnell Ave, Fort Wayne, IN 46805-1414
5
Start:Lakeside Park & Rose Garden
Fort Wayne, Indiana·
4.5
(96) review
1401 Lake Ave, Fort Wayne, IN 46805
6
Start:Amherstburg Navy Yard National Historic Site
Amherstburg, Ontario·
5.0
(94) review
Dalhousie Street, Amherstburg, Ontario N9V 1W7 Canada
7
Start:Sprucewood Shores Estate Winery
Harrow, Essex, Ontario·
4.5
(97) review
The Sprucewood Family warmly welcomes you to sample handcrafted 100% Ontario VQA wines at Ontario's only beachfront destination vineyard, winery and tasting room. We are situated on 45 Acres with access to gardens, a sandy beach, and picnic tables. Enjoy a glass of wine with a picnic basket and explore our grounds year round. Tasting room open 7 days a week 11am - 5pm (we occasionally close early due to special events. Please check our social media for daily updates @sprucewoodshores)
8
Start:Rock & Roll Hall of Fame
Cleveland, Ohio·
4.5
(9964) review
Headquartered in a boldly designed building on Lake Erie's shore, The Rock and Roll Hall of Fame is a 150,000-square-foot museum featuring ever-changing exhibits documenting the history of rock and roll, from Elvis to our days. You’ll see hundreds of original artifacts, from Jimi Hendrix outfits to The Beatles’ handwritten lyrics. Experience the excitement of a Rock Hall induction night at the Power of Rock Experience or have your very own jam session at the Garage. You can also watch a concert while you're here, so check out the Rock Hall’s schedule and plan ahead. – Tripadvisor
9
Start:Federal Reserve Bank of Cleveland: Education and Learning Center
Cleveland, Ohio·
4.5
(95) review
Ever wonder how money works or what the Federal Reserve Bank of Cleveland does as part of the central bank of the US? Visit our Education and Learning Center featuring more than 25 fun, hands-on exhibits that answer these questions and more! We have interactive games, visual exhibits, creative stations, and illuminating films that explain everything about money you can think of, from how we use it, to why it looks the way it looks. Come see our historic lobby, take pictures with our money tree, trade coconuts on Barter Island, identify counterfeit bills, and even make your own money! All this in the heart of Cleveland, just steps away from downtown attractions. Admission is free and photos are welcome.
10
Start:Museum of Contemporary Art Cleveland
Cleveland, Ohio·
3.5
(93) review
11400 Euclid Ave, Cleveland, OH 44106-3926
11
Start:Lock 3
Akron, Ohio·
4.5
(98) review
200 S Main St, Akron, OH 44308-1315
12
Start:Paladin Brewing
Austintown, Youngstown, Ohio·
4.5
(9) review
6520 Mahoning Ave, Austintown, Youngstown, OH 44515-2012
13
Start:Hollywood Gaming Mahoning Valley Race Course
Youngstown, Ohio·
3.5
(83) review
655 N Canfield Niles Rd, Youngstown, OH 44515-1102
14
Start:Basilica of Our Lady of Mount Carmel
Youngstown, Ohio·
4.5
(7) review
343 Via Mount Carmel Ave, Youngstown, OH 44505-3037
15
Start:What Lifts You Mural
Nashville, Davidson County, Tennessee·
4.5
(83) review
You can find one of the town’s most famous photo ops in The Gulch neighborhood—a pair of intricate white lace wings against a black wall. There's usually a line, so go early in the morning or late in the day for fewer crowds. Try to find the easter eggs that the artist put into the mural: a cowboy hat, guitars, and barbecues to represent Nashville. Explore other street art in Nashville on a mural art tour—you'll see lots of other great sights, with plenty of time for photo ops.
16
Start:ScareHouse
Pittsburgh, Pennsylvania·
4.0
(87) review
Pittsburgh Zombies love shopping malls – and we think you will love our NEW, larger, and permanent home inside the Galleria at Pittsburgh Mills. Thank You Pittsburgh for supporting us for more than 20 years of fears! ScareHouse has been ranked as one of “America’s Scariest Halloween Attractions” by Travel Channel and has been featured on Good Morning America, USA TODAY, The Daily Show and many other national media outlets.
17
Start:Marine Corps League NE Detachment Museum
Scranton, Pennsylvania·
5.0
(8) review
1340 Alder Street, Scranton, PA
18
Start:Allentown Rose Gardens
Allentown, Pennsylvania·
4.5
(78) review
3000 Parkway Blvd, Allentown, PA 18104-5327
19
Start:Mack Trucks Historical Museum
Allentown, Pennsylvania·
4.5
(95) review
2402 Lehigh Pkwy S, Allentown, PA 18103-2900
20
Start:Accomplice New York
New York City, New York·
4.5
(987) review
This comedic interactive experience sends you on a mission to assist a bunch of ex-cons lookin’ to skip town. The journey starts near the South Street Seaport and works its way up through some of New York City's most colorful neighborhoods. Several alcoholic beverages and light appetizers are included during this three hour journey. For private groups, you can book up to 15 people. Basic pricing per person is $85.00. Accomplice also runs a Village show, a Chelsea show and a traveling meal, each with its own characters and story line. For more information, please visit our website!
21
Start:BrainXcape
New York City, New York·
5.0
(99) review
160 Broadway 3rd Fl, New York City, NY 10038
22
Start:Precision NY Chauffeur & Airport Transportation Services
New York City, New York·
5.0
(99) review
Here at Precision NY Chauffeur & Airport Transportation Service, we offer limousine service and point to point transportation NYC. You can always depend on us for reliable transportation New York, New Jersey, Westchester, Connecticut, Washington DC, Pennsylvania, and Boston. Along with equitable rates and attentive service, we offer transfer services anywhere within the country. For your convenience, you may reserve any vehicle from our fleet vehicles up to 24 hours in advance, including the Lincoln MKT, Lincoln Town Car and Cadillac XTS. For larger parties or a more comfortable ride, we have Cadillac™ Escalades, Lincoln™ Navigators, and Chevy™ Suburbans. We also carry New 2023 and 2024 Mercedes S560s.
23
Start:The Blue Bar, Algonquin Hotel
New York City, New York·
4.0
(99) review
Comfortable and classic, the lounge of the Algonquin Hotel is a New York landmark.
24
Start:Daniel Roy's Parlour Of Deceptions
New York City, New York·
5.0
(99) review
Join magician Daniel Roy at the exclusive Salmagundi Club of New York City for an evening of sleight-of-hand, misdirection, and magic. Limited to just 40 guests, this is an intimate experience of wonder. While this is not a kids show and the magic is geared towards adults, the performance is entirely “clean” and appropriate for audience members age 13 years and older.
CHECKLIST
GPS device or app
Download Offline Map
Car charger and portable battery
Water bottles and snacks
Travel pillow and blanket
Sunglasses and sunscreen
First-aid kit
Trash bags
Hand sanitizer and wet wipes
Driver’s license and vehicle registration
Cash and cards
Camera or smartphone
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Frequently Asked Questions
What's the driving distance between Chicago and Staten Island?
The distance is 792 miles
What's the travel time between Chicago and Staten Island?
The driving time can vary depending on traffic conditions, but it is typically 15h 0m mins in normal traffic
What are some of the best cities to visit between Chicago and Staten Island?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Staten Island?
There are plenty! Here are some stops you shouldn’t miss on your way to Staten Island
What’s the weather like in Staten Island?
The weather in Staten Island is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Staten Island in January
Weather in Staten Island in February
Weather in Staten Island in March
Weather in Staten Island in April
Weather in Staten Island in May
Weather in Staten Island in June
Weather in Staten Island in July
Weather in Staten Island in August
Weather in Staten Island in September
Weather in Staten Island in October
Weather in Staten Island in November
Weather in Staten Island in December
Interested in a detailed plan for your time in Staten Island?
Plan your dream Staten Island trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Staten Island
A 2-day itinerary in Staten Island
A 3-day itinerary in Staten Island
A 4-day itinerary in Staten Island
A 5-day itinerary in Staten Island
A 6-day itinerary in Staten Island
Where else can I travel to if I'm starting my trip in Chicago?
We have a lot of great trip options for Chicago! See the links below for all the itineraries we created for you
